Publication: Synthesis of bridged biarylbisquinones and effects of biaryl dihedral angles on photo- and electro-chemical properties
1
Issued Date
2016-03-24
Resource Type
ISSN
14645416
00404020
00404020
Other identifier(s)
2-s2.0-84958885578
Rights
Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
Tetrahedron. Vol.72, No.12 (2016), 1533-1540
Suggested Citation
Krittaphat Wongma, Nantiya Bunbamrung, Tienthong Thongpanchang Synthesis of bridged biarylbisquinones and effects of biaryl dihedral angles on photo- and electro-chemical properties. Tetrahedron. Vol.72, No.12 (2016), 1533-1540. doi:10.1016/j.tet.2016.02.001 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/43111
Research Projects
Organizational Units
Authors
Journal Issue
Thesis
Title
Synthesis of bridged biarylbisquinones and effects of biaryl dihedral angles on photo- and electro-chemical properties
Other Contributor(s)
Abstract
© 2016 Elsevier Ltd. All rights reserved. A series of bridged biarylbisquinones, QBINOLs 1-4, and their corresponding monomers, QNaphs 5-6, were designed to demonstrate the influence of biaryl conformation on the photo- and electro-chemical properties of the molecules. All target compounds were synthesized from the Diels-Alder reaction between silyl enol ethers of the corresponding naphthyl or binaphthyl derivatives and p-benzoquinone. Addition of an OMe auxochrome or formation of the dimeric structures affect the absorption spectra and the energy band gap (Eg), but not the reduction potentials of the molecules. Narrowing the dihedral angles of the QBINOLs by shortening methylene bridges limited the contribution of bridging OR auxochromes and therefore resulted in lower HOMO levels and larger Eg.
